Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use
2-(4-Chlorophenyl)-5-benzoxazoleacetic acid (CBA) and its ester, methyl-2-(4-chloro-phenyl)-5-benzoxazoleacetate (MCBA), were synthesized, and their structures were confirmed by <sup>1</sup>HNMR, IR, and mass spectrophotometry. The anti-psoriatic activities of CBA and MCBA were tested us...
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MDPI AG
2022-05-01
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| Online Access: | https://www.mdpi.com/1420-3049/27/9/3023 |
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| author | Rami Ayoub Jamal Jilani Qais Jarrar Raad Alani Chrismawan Ardianto Khang Wen Goh Dalia Ali Said Moshawih |
| author_facet | Rami Ayoub Jamal Jilani Qais Jarrar Raad Alani Chrismawan Ardianto Khang Wen Goh Dalia Ali Said Moshawih |
| author_sort | Rami Ayoub |
| collection | DOAJ |
| description | 2-(4-Chlorophenyl)-5-benzoxazoleacetic acid (CBA) and its ester, methyl-2-(4-chloro-phenyl)-5-benzoxazoleacetate (MCBA), were synthesized, and their structures were confirmed by <sup>1</sup>HNMR, IR, and mass spectrophotometry. The anti-psoriatic activities of CBA and MCBA were tested using an imiquimod (IMQ)-induced psoriatic mouse model, in which mice were treated both topically (1% <i>w/w</i>) and orally (125 mg/kg) for 14 days. The erythema intensity, thickness, and desquamation of psoriasis were scored by calculating the psoriasis area severity index (PASI). The study also included the determination of histopathological alterations in the skin tissues of treated mice. Topical and oral administration of CBA and MCBA led to a reduction in erythema intensity, thickness, and desquamation, which was demonstrated by a significant decrease in the PASI value. In addition, skin tissues of mice treated with CBA and MCBA showed less evidence of psoriatic alterations, such as hyperkeratosis, parakeratosis, scale crust, edema, psoriasiform, and hyperplasia. After administration of either topical or oral dosing, the anti-psoriatic effects were found to be stronger in MCBA-treated than in CBA-treated mice. These effects were comparable to those produced by Clobetasol propionate, the reference drug. This drug discovery could be translated into a potential new drug for future clinical use in psoriasis treatment. |
| first_indexed | 2024-03-10T03:52:30Z |
| format | Article |
| id | doaj.art-3725ef8fecc64253aa27f0ff07396c25 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:52:30Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3725ef8fecc64253aa27f0ff07396c252023-11-23T08:53:04ZengMDPI AGMolecules1420-30492022-05-01279302310.3390/molecules27093023Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical UseRami Ayoub0Jamal Jilani1Qais Jarrar2Raad Alani3Chrismawan Ardianto4Khang Wen Goh5Dalia Ali6Said Moshawih7Department of Applied Pharmaceutical Sciences and Clinical Pharmacy, Faculty of Pharmacy, Isra University, Amman 11622, JordanDepartment of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, Irbid 22110, JordanDepartment of Applied Pharmaceutical Sciences and Clinical Pharmacy, Faculty of Pharmacy, Isra University, Amman 11622, JordanDepartment of Physiotherapy, Faculty of Allied Medical Sciences, Isra University, Amman 11622, JordanDepartment of Pharmacy Practice, Faculty of Pharmacy, Universitas Airlangga, Surabaya 60115, IndonesiaFaculty of Data Science and Information Technology, INTI International University, Nilai 71800, MalaysiaDepartment of Physiotherapy, Faculty of Allied Medical Sciences, Isra University, Amman 11622, JordanPAP Rashidah Sa’adatul Bolkiah Institute of Health Sciences, Universiti Brunei Darussalam, Gadong BE1410, Brunei2-(4-Chlorophenyl)-5-benzoxazoleacetic acid (CBA) and its ester, methyl-2-(4-chloro-phenyl)-5-benzoxazoleacetate (MCBA), were synthesized, and their structures were confirmed by <sup>1</sup>HNMR, IR, and mass spectrophotometry. The anti-psoriatic activities of CBA and MCBA were tested using an imiquimod (IMQ)-induced psoriatic mouse model, in which mice were treated both topically (1% <i>w/w</i>) and orally (125 mg/kg) for 14 days. The erythema intensity, thickness, and desquamation of psoriasis were scored by calculating the psoriasis area severity index (PASI). The study also included the determination of histopathological alterations in the skin tissues of treated mice. Topical and oral administration of CBA and MCBA led to a reduction in erythema intensity, thickness, and desquamation, which was demonstrated by a significant decrease in the PASI value. In addition, skin tissues of mice treated with CBA and MCBA showed less evidence of psoriatic alterations, such as hyperkeratosis, parakeratosis, scale crust, edema, psoriasiform, and hyperplasia. After administration of either topical or oral dosing, the anti-psoriatic effects were found to be stronger in MCBA-treated than in CBA-treated mice. These effects were comparable to those produced by Clobetasol propionate, the reference drug. This drug discovery could be translated into a potential new drug for future clinical use in psoriasis treatment.https://www.mdpi.com/1420-3049/27/9/3023synthesisarylbenzoxazolepsoriasisimiquimodin vivoprodrug |
| spellingShingle | Rami Ayoub Jamal Jilani Qais Jarrar Raad Alani Chrismawan Ardianto Khang Wen Goh Dalia Ali Said Moshawih Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use Molecules synthesis arylbenzoxazole psoriasis imiquimod in vivo prodrug |
| title | Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use |
| title_full | Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use |
| title_fullStr | Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use |
| title_full_unstemmed | Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use |
| title_short | Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use |
| title_sort | synthesis and in vivo evaluation of benzoxazole derivatives as promising anti psoriatic drugs for clinical use |
| topic | synthesis arylbenzoxazole psoriasis imiquimod in vivo prodrug |
| url | https://www.mdpi.com/1420-3049/27/9/3023 |
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